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Alcohols Phenols and Ethers question

2019 · 12 Jan · Shift 1 · Q16
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Alcohols Phenols and Ethers question

2019 · 12 Jan · Shift 1 · Q16

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
JEE Main 2019 (Online) 12th January Morning Slot Chemistry - Alcohols, Phenols and Ethers Question 132 English can not be prepared by -
  1. A
    CH3CH2COCH3CH_3CH_2COCH_3CH3​CH2​COCH3​ + PhMgX
  2. B
    PhCOCH3PhCOCH_3PhCOCH3​ + CH3CH2MgXCH_3CH_2MgXCH3​CH2​MgX
  3. C
    PhCOCH2CH3PhCOCH_2CH_3PhCOCH2​CH3​ + CH3MgXCH_3MgXCH3​MgX
  4. D
    HCHOHCHOHCHO + PhCH(CH3)CH2MgXPhCH(CH_3)CH_2MgXPhCH(CH3​)CH2​MgX
View written solutionFree

Correct answer: D

We need to identify which reagent pair cannot prepare the same alcohol.

1. General rule: Grignard addition to carbonyl compounds

Grignard reagents add to carbonyl compounds, and after hydrolysis:

  • Aldehyde or ketone carbon gets attached to the alkyl/aryl group of Grignard reagent.
  • The carbonyl carbon becomes the carbon bearing the OHOHOH group.

So, for each option, let us write the alcohol formed.


2. Evaluate each option

Option A: CH3CH2COCH3+PhMgXCH_3CH_2COCH_3 + PhMgXCH3​CH2​COCH3​+PhMgX

The ketone is CH3CH2COCH3CH_3CH_2COCH_3CH3​CH2​COCH3​ (2-butanone).

Addition of PhMgXPhMgXPhMgX gives: CH3CH2C(OH)(Ph)CH3CH_3CH_2C(OH)(Ph)CH_3CH3​CH2​C(OH)(Ph)CH3​ So the product is: Ph−C(OH)(CH3)(CH2CH3)Ph-C(OH)(CH_3)(CH_2CH_3)Ph−C(OH)(CH3​)(CH2​CH3​)


Option B: PhCOCH3+CH3CH2MgXPhCOCH_3 + CH_3CH_2MgXPhCOCH3​+CH3​CH2​MgX

The ketone is acetophenone, PhCOCH3PhCOCH_3PhCOCH3​.

Addition of CH3CH2MgXCH_3CH_2MgXCH3​CH2​MgX gives: PhC(OH)(CH3)(CH2CH3)PhC(OH)(CH_3)(CH_2CH_3)PhC(OH)(CH3​)(CH2​CH3​)

This is the same alcohol as in A.


Option C: PhCOCH2CH3+CH3MgXPhCOCH_2CH_3 + CH_3MgXPhCOCH2​CH3​+CH3​MgX

The ketone is propiophenone, PhCOCH2CH3PhCOCH_2CH_3PhCOCH2​CH3​.

Addition of CH3MgXCH_3MgXCH3​MgX gives: PhC(OH)(CH3)(CH2CH3)PhC(OH)(CH_3)(CH_2CH_3)PhC(OH)(CH3​)(CH2​CH3​)

Again, this is the same alcohol.


Option D: HCHO+PhCH(CH3)CH2MgXHCHO + PhCH(CH_3)CH_2MgXHCHO+PhCH(CH3​)CH2​MgX

Formaldehyde with a Grignard reagent gives a primary alcohol of the form: RCH2OHRCH_2OHRCH2​OH

Here R=PhCH(CH3)CH2−R = PhCH(CH_3)CH_2-R=PhCH(CH3​)CH2​−, so product is: PhCH(CH3)CH2CH2OHPhCH(CH_3)CH_2CH_2OHPhCH(CH3​)CH2​CH2​OH

This is a primary alcohol, not the tertiary alcohol formed in A, B, and C.


3. Conclusion

Options A, B, and C all give the same tertiary alcohol: PhC(OH)(CH3)(CH2CH3)PhC(OH)(CH_3)(CH_2CH_3)PhC(OH)(CH3​)(CH2​CH3​)

Option D gives a different primary alcohol: PhCH(CH3)CH2CH2OHPhCH(CH_3)CH_2CH_2OHPhCH(CH3​)CH2​CH2​OH

Hence, the required alcohol cannot be prepared by D.

4. Comparison with stored answer

Stored correct answer: D

My derived answer: D

So, the derived answer agrees with the stored answer.

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